5-Substituted-pyrazolo(4,3-c)pyridines

Abstract

Compounds of the formula ##SPC1## Their N-oxides and acid addition salts thereof are provided which have been found to possess anti-inflammatory activity. In addition, methods for preparing such compounds, pharmaceutical compositions containing such compounds, and methods for using such compositions as anti-inflammatory agents are also provided.

What is claimed is: 
     
       1. A compound of the formula ##SPC6## wherein X 1  and X 2  are the same or different and are selected from the group consisting of hydrogen, F, cl, lower alkyl, lower alkoxy, or CF 3  ; R is selected from the group consisting of hydrogen, lower alkyl, phenyl lower alkyl, x 1  or 2 -  substituted phenyl lower alkyl wherein X 1  or 2 is as previously defined, hydroxy lower alkyl or lower alkanoyl; R 1  and R 2  are the same or different and are selected from the group consisting of hydrogen or lower alkyl or ##EQU16## may be taken together to form a 5- or 6-membered heterocyclic ring which may include one other heteroatom selected from the group consisting of sulfur, nitrogen or oxygen; and n is 0 to 4; and N-oxides and pharmaceutically acceptable acid addition salts thereof.   
     
     
       2. A compound as defined in claim 1 wherein X 1  and X 2  are the same. 
     
     
       3. A compound as defined in claim 1 wherein X 1  and X 2  are hydrogen. 
     
     
       4. A compound as defined in claim 1 wherein one of X 1  and X 2  is hydrogen. 
     
     
       5. A compound as defined in claim 1 wherein X 1  and X 2  are the same or different and are selected from the group consisting of hydrogen, lower alkyl, F or Cl. 
     
     
       6. A compound as defined in claim 1 wherein X 1  and X 2  are the same or different and are selected from the group consisting of hydrogen, lower alkoxy or CF 3 . 
     
     
       7. A compound as defined in claim 1 wherein R is selected from the group consisting of hydrogen and lower alkyl. 
     
     
       8. A compound as defined in claim 7 wherein R is selected from the group consisting of hydrogen, lower alkyl, and hydroxy lower alkyl. 
     
     
       9. A compound as defined in claim 1 wherein R is phenyl lower alkyl or X 1  or 2 -substituted phenyl lower alkyl. 
     
     
       10. A compound as defined in claim 1 wherein n is 0, 1 or 2. 
     
     
       11. A compound as defined in claim 10 wherein X 1  and X 2  are hydrogen, and R is methyl. 
     
     
       12. A compound of claim 1 having the name 2,3,3a,4,6,7-hexahydro-N-2-dimethyl-3-phenyl-7-(phenylmethylene)-5H-pyrazolo-[4,3-c]pyridine-5-carboxamide. 
     
     
       13. A compound as defined in claim 1 having the name 2,3,3a,4,6,7-hexahydro-2-methyl-3-phenyl-7-(phenylmethylene)-5H-pyrazolo[4,3-c]pyridine-5 carboxamide. 
     
     
       14. A compound as defined in claim 1 having the name 5-[(dimethylamino)acetyl]-3,3a,4,5,6,7-hexahydro-2-methyl-3-phenyl-7-(phenylmethylene)-2H-pyrazolo[4,3-c]pyridine. 
     
     
       15. A compound as defined in claim 1 having the name 5-[3-(Dimethylamino)propionyl]-3,3a,4,5,6,7-hexahydro-2-methyl-3-phenyl-7-(phenylmethylene)-2H-pyrazolo-[4,3-c]pyridine. 
     
     
       16. A compound of claim 1 wherein ##EQU17## is selected from the group consisting of piperidino, pyrrolidino, morpholino, thiamorpholino, piperazino and N-lower alkyl piperazino.